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Troublesome Quest Models

by Mike on 19 July 2021

Quest models are frameworks you can use to build interesting quests and adventures in your D&D games. There are a number of common and self-evident quest models we can use when building our own adventures. Here are a few examples:

There are many others, some more complicated. I'm a big fan of the "heist" model in which the characters must steal something from a guarded place because it's built around a situation and lets the players choose their approach. It's perfect situation-based D&D. I'm also a huge fan of the Seven Samurai model in which the characters defend a village from marauders. You can change this model in lots of ways and still have an interesting adventure that, like the heist, is built around the approach of the characters.

Some common models seem like good ideas, though, but often fall apart in play. These include:

We see quests like this often because they're so common in popular fiction. Chases, mysteries, escape from being captured; these are all common stories that should fall right into our D&D games, but why don't they work?

All of them tend not to work for a few reasons:

  1. They assume the characters act a certain way.
  2. They often remove character agency.

Many times these quests rely on the characters doing something in just the right way for the story to go forward. Sometimes, in order to ensure that the quest goes that way, the adventure forces them. You can run, but not too fast or you gain exhaustion. You can stay where you are but if you do, you'll be overwhelmed and killed off-screen. You can fight the adult blue dragon but if you do, she'll kill you with one blow.

The tricky part is that sometimes these models can work. We see them often enough and they don't always fall flat, but, I argue, it's much harder to get these quests to work well than more open-ended quests with a greater opportunity for character agency and multiple paths.

Often these troublesome quest models work fine if they happen organically. Yes, bosses can escape, but they may not. Yes, you might have to chase someone or something but you might catch up quickly or it might get away. You might end up facing an insurmountable villain early or they might take your stuff and you have to retrieve it. All of these things work much better if they happen as a course of the story. They fall apart, however, when they're the expectation and not the result of the character's actions.

Better are resilient quests offering multiple options and paths. Think about how many ways the heist or village defense quests can go.

Resilient quests offer meaningful choices and options to the players and work regardless of which choice they make. Brittle quest models fall apart if the characters don't act a certain way.

Note that, for the sake of this article, I'm using the term "quests" loosely. In many cases these are more like encounters than quests. Sometimes they're full-length adventures, sometimes just a scene in a larger context. Forgive the misuse of the term quest when it doesn't fit.

Here are some examples of brittle quests often requiring the characters to act a certain way or remove character agency to move the story forward.


Page 252 of the Dungeon Master's Guide includes rules for a chase, as does chapter 4 of Waterdeep Dragon Heist. How can this quest model be bad if they're baked into D&D? Let's look at a quote from Waterdeep Dragon Heist:

The Stone of Golorr possesses an intelligent, alien intellect and has enough prescience to realize that the characters are destined to find it. The stone doesn't want to be found too easily, though.

If the characters obtain the stone earlier than expected, it proves uncooperative and tries to separate itself from the party as quickly as possible, refusing to share any knowledge with characters in the meantime.

This is the problem with a chase. You need things to go just right to keep the chase going. What if the characters use misty step and grab the stone too early? The stone decides it doesn't want to be caught. Lame. What if the characters take a long rest before the chase begins? Does the chase stop until the characters start chasing it again?

Forcing a chase is one of the worst forms of railroading. It requires characters to act exactly a certain way so they don't finish the chase too early or not at all.

Fixing the chase. Chases, when they do occur, should happen naturally at the table, and not be planned ahead of time. Anytime you think a chase might happen, ask yourself if the chase will work if it ends quickly or never gets followed at all. The chase is a tool you can use when the situation happens spontaneously but planning one out usually ends in ways you can't plan for.

Capture and Escape

Another common story in fiction, escape seems like it should be a great story idea for our D&D games. The problem comes with the capture. Players, generally, hate losing and if you have to throw an overwhelming force at them to get them to lose, they'll hate that too. Worse, they may find a way to circumvent it or, even worse than that, half of them will find a way to avoid capture while the other half are captured. Good luck running that situation.

Throwing an overwhelming force at your characters just to stick them in a jail cell isn't going to be as much fun as you think.

Fixing Escape Quests. Escaping capture only works if the characters begin in captivity and, I'd argue, this only works well if the players know ahead of time that they'll begin captured. This, for example, is the way Out of the Abyss starts and I know if I ran it again, I'd ensure, during my session zero, that the players know they begin enslaved by the drow.

Being captured as part of the ongoing story is a fine way to handle a potential total-party-kill, should it happen. Being captured isn't a problem if it happens organically during the game. Forcing the characters to be captured sucks.

Solving Predefined Mysteries

Mysteries, like the other quests here, have centuries of history in our fiction so surely they make for a fun D&D game, right?

Not so much.

Like chases, many mysteries assume the characters find the right clues at the right time to figure out the mystery only when the time is right. All too often the characters either figure it out right away or miss the vital clues completely. What happens during the rest of the adventure if a character figures it out and stabs the murderer in the first scene? What do you do with the other 3.5 hours of the adventure?

Fixing the mystery. Like other solutions described in this article, a mystery can work well as long as you don't make assumptions about what the characters learn and when they'll learn it. Mysteries can work well as situations as long as how the characters find the right clues isn't pre-defined. Justin Alexander, for example, recommends the three clues style, in which you ensure that, for any vital piece of information, three clues exist. My own secrets and clues approach gives you ten secrets or clues that can drop into the game anywhere which will, eventually, lead to the discovery you want the characters to find. If your mystery depends on the characters finding the right things the right way at the right time, it's probably too brittle.

All-or-Nothing Collection Quests

The cult of the dragon needs the five dragon masks to summon Tiamat. The characters need the nine puzzle cubes to open the door to the Tomb of the Nine Gods. These seem like nice and clean quest models except for one big problem. What happens if the characters get just one of the masks and throws it into the ocean? What if the Red Wizards of Thay get one of the puzzle cubes and hide it in Szass Tam's fanny pack? You're screwed. Now you have to force some sort of heist, either by the characters or the villains depending on who needs it. All-or-nothing quests are brittle because just one item falling into the wrong hands ends the whole quest. It forces DM to contrive situations just so the quest can continue.

Fixing the all-or-nothing quest. My solution to the all-or-nothing collection quest is the three of five collection quest model. If you need only the majority of items to succeed, now things get interesting. The opposing side must collect more than half to thwart the other side. It becomes a race with many different paths and many different options. You can see more about this in my three of five collection quest Youtube video.

Facing Insurmountable Bosses

Another common trope is the early face-off with the insurmountable foe. Hoard of the Dragon Queen commits this sin twice in the first chapter. The characters, 1st or 2nd level, find themselves face to face with an adult blue dragon. How exactly is that encounter supposed to go? Why wouldn't the dragon just kill them? What are the characters supposed to do? What options to they have? Groveling and hoping for a high persuasion check is about it.

Big villains are rare so low level characters aren't likely to run into them. Best keep powerful bosses for powerful characters.

Strahd is an exception. He loves to personally check out the fresh meat.

Solving Puzzles

A lot of DMs likely disagree with me on this one but I'm not a fan of puzzles. First, they're hard to prep; definitely not lazy. Second, they rarely make sense. Why would anyone spend the time and energy to protect something with a puzzle? Why not just put a good lock in place? Do they have to navigate their own bullshit puzzle every time they want to make a withdrawal?

Puzzles also often fail in gameplay. Rarely are all players invested in a puzzle and those that aren't quickly grab onto their phones. Stick to the core mechanics and gameplay of D&D and leave puzzles aside.

Recovering Stolen Stuff

Likely every DM makes this mistake at least once in their lives. What better motivation for the characters than recovering their stolen gear? The problem is that loss aversion is real and players hate it when their stuff gets stolen. They also don't feel good even when they get it back. They feel like they're back where they started. Don't steal the characters' stuff.

Dream Sequences and Flashbacks

Another common quest model, why not show some history with a flashback or take the game into a new dimension with a dream sequence? The problem is that the characters usually end up where they started only three hours later. The characters don't get much from these. They don't really have agency. They can't change history. It's usually the longest lore dump ever. Skip dream sequences or flashbacks unless you have a really good reason and the characters have some agency over the situation.

Exception: a cool Inception-style dream heist might be a lot of fun. You might also use a dream sequence or flashback as a way to write history by the actions of the characters. Like the players deciding the location of the key items in i6 Ravenloft or Curse of Strahd, they might define things by their actions and choices in the past.

Escaping Villains

Like losing gear, watching villains run off too often sucks, particularly when the characters know there was no way to stop it from happening. It's one thing if a villain manages to escape on their own. It's something else when the DM forces the issue. Lichs and vampires have built-in escape options so they're an exception. Otherwise, forcing a villainous escape feels lame.


Here's another bad idea DMs often try once. When trusted NPCs betray the characters, you're breaking trust with the players. The same is true when one of the player characters betrays the rest of the party and the DM is in on it. It seems fun and exciting but it's really just lame. It breaks trust all around the table and that's not fun and won't lead the game in the right direction. Avoid betrayals.

There are clear exceptions to this rule when the players know there's betrayal going on and it's all discussed and agreed upon in a session zero.


DMs often love tinkering with the mechanics in D&D. Why not have an entire vehicle sub-system or a whole mechanical subsystem for handling complex rituals? What about a system for running a bar or piloting an airship?

The problem with subsystems is that often the mechanics don't work nearly as well as the rest of the game. Players don't want to learn them because they know they're temporary. You also don't really need them. Ability checks cover just about anything you need to do in the game. Anyone who remembers the Mako from Mass Effect knows what I'm talking about. The players are invested in their characters and the existing mechanics of D&D. Let them focus on that instead of having to learn new and buggy subsystems for things an ability check likely covers.

Use Flexible Quest Models

When you seek quest models to build your D&D adventures, seek those offering robust and flexible options for your adventures. Find those that build off of situation-based adventures in which the characters have meaningful options and multiple solutions. Use quest models where even you have no idea how they'll play out at the table. As for these troublesome quest models? Let them happen if that's how the story evolves but don't use them as an incoming assumption ahead of time.

Keep flexible quest models in your bag of tricks and run awesome open-ended adventures with your friends. Play to see what happens.

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